Acetyl chloride → a-Hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid, methyl ester

Beteiligte Stoffe

Reaktionsschritte

As shown in Scheme IV, in this method, adamantyl bromide (Formula A) is alkylated via zinc chloride catalysis to produce <a-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid (Formula B). <a-Hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid (Formula B) is then esterified using acetyl chloride in methanol to produce <a-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid, methyl ester (Formula C). <a-Hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid, methyl ester (Formula C) is then converted to <a-oxotricyclo[3.3.1.13,7]decane-1-acetic acid, methyl ester (Formula D) by Swern oxidation. <a-Oxotricyclo[3.3.1.13,7]decane-1-acetic acid, methyl ester (Formula D) is then hydroxylated to form 3-hydroxy-<a-oxotricyclo[3.3.1.13,7]decane-1-acetic acid, methyl ester (Formula I), which is then hydrolyzed to form 3-hydroxy-<a-oxotricyclo[3.3.1.13,7]decane-1-acetic acid (Formula II). Also see Examples 21 through 25 herein.

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